Salicylamide → 2-(Cyclopropylmethoxy)benzamide

HRID 703423Notes

Reaction equation

HRID 703423 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[OH-].[Na+].Br[CH2:14][CH:15]1[CH2:17][CH2:16]1>C(O)C>[CH:15]1([CH2:14][O:1][C:2]2[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([NH2:6])=[O:5])[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 5147SalicylamideHCID 14798Sodium HydroxideHCID 81503Bromomethylcyclopropane

Product 1

HCID 27280292-(Cyclopropylmethoxy)benzamideYield 60.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Hydroxybenzamide (5.17 g, 37.74 mmol) and sodium hydroxide (1.5 g, 37.5 mmol) in ethanol (20 ml) were refluxed for 1 h to give a clear solution. (Bromomethyl)cyclopropane (5.09 g, 37.7 mmol) was added and the mixture refluxed for 36 h. The solvent was evaporated and the residue triturated thoroughly with ether and water to give the above compound (4.37 g).

Workup

  1. customto give a clear solution
  2. temperaturethe mixture refluxed for 36 h
  3. customThe solvent was evaporated
  4. customthe residue triturated thoroughly with ether and water

Sources & evidence

ORD record
ord-011d24b890b04776bdf69dfcb8243399
Source dataset
uspto-grants-1991_01
Patent number
US04983600

Reaction notes

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